Inmates returning to the community engage in elevated rates of risky behavior, including: drug use, HIV-risk- behavior, and crime. This harmful risky behavior is relevant not only to the health and well being of offenders but also to the general public. Theory and empirical evidence indicate that impulsivity is strongly associated with multiple types of harmful risky behavior (Gottfredson & Hirschi, 1990; Verdejo Garcia et al., 2008). Additionally, research finds that psychological distress may exacerbate impulsivity (Muraven et al., 1998; Baumeister et al., 1998; Heatherton, 2000), resulting in Distress Driven Impulsivity (DDI). Individual differences in the tendency to experience DDI assessed by self-report measures, have been repeatedly correlated with harmful risky behavior in college, community, and patient samples (Cyders et al., 2008). Self-report measures, however, can be limited by respondents' lack of insight and positive impression management (Lejuez et al., 2002; Dougherty et al., 2003). Although less frequently used in current research, computer-based behavioral measures may provide a superior measurement of DDI to that of self-report. The principle aim of the proposed study is to investigate DDI as a predictor of harmful risky behavior above and beyond impulsivity. The proposed study would administer measures of impulsivity and DDI using both computerized-behavioral measures (the IMT: Dougherty et al., 2005, the BART: Lejeuz et al., 2002; Mirror Tracing Persistence Task; Daughters et al., 2005) and self-report (the UPPS; Whitside & Lynam, 2001) in a sample of 70 adult male inmates nearing release into the community from a county jail. Analyses will examine the degree to which DDI predicts harmful risky behavior at 3 months and 1 year post-release above and beyond measures of self-report and computer-based behavioral impulsivity. Additionally, this study aims to (1) examine the incremental validity of computer-based behavioral measures of impulsivity above and beyond self-report measures of impulsivity in the prediction of subsequent harmful risky behavior and (2) to investigate the relationship between different dimensions of impulsivity with different types of harmful risky behaviors. The long-term aim of this research is to identify a new, more clearly articulated target for treatment, with the ultimate goal of reducing post-release drug use, HIV-risk-behavior, and recidivism in this vulnerable, high risk, understudied, and underserved population.